I've spent over $10,000 this year on dating — matchmaking, coaching, paid apps. The constant feedback I get is "stop dating, focus on making money, grow your business." My answer is that I'm not choosing between them. The money I put into dating is helping me build my business and my income, because for me the two are inseparable.
Dating is the hardest area — and that's the point
I got divorced in December 2025, and dating has been the single most emotionally painful part of my life since. That's almost funny, because I recently made a video about feeling rich with a negative $200,000 net worth while burning around $5,000 a month — and the money isn't what hurts. I have complete confidence I can make money; I've done it before. Dating is where I'm actually building character. Getting wrecked emotionally out there has made me far more resilient, and that resilience carries straight into my business. Eight months ago a cancellation would have leveled me; now getting ghosted barely moves me. That solidity shows up in how I run everything else.
Why I put dating coaching on a business card
Last night I paid $1,200 for a friend to coach me on dating — and I said no to another friend's $4,500 three-month package. I put the $1,200 on my business credit card on purpose, because it isn't only dating help: it includes photos that update my channels, and the whole experience becomes stories and material I can use. The better I get at dating, the more it translates into the business. It's one budget serving two goals that aren't really two goals.
A day that proves the loop
Here's how it actually plays out. I went to the pier for a photo shoot with a friend — fun, lighthearted, a genuinely great time. Coming off that high, I stopped by my Alcoholics Anonymous meeting, caught one of my guys right after it ended, and we talked for two and a half hours about his life. He's stuck in a job out of fear and, I think, right on the edge of a breakthrough. On the surface someone would ask why I'm not home filming and making money instead. But that conversation is the mission — waking people up and helping them feel empowered. I went home feeling like I'd won the whole day, and woke up the next morning completely clear on exactly what to build next.
The dating self and the business self are the same self
That's the whole thesis. The part of me that's dating is not separate from the part of me that's building a business. My excitement about finding a wife and having more kids is fuel — and the business is what supports that family. The love and validation my audience gives me makes me more confident going on dates, and having fun on those dates leaves me inspired to create. It's one loop, not two ledgers. Investing in dating is investing in the business.
This is the flip side of spending $10,000 dating and still being single — same money, viewed as an investment in who I'm becoming. If this resonates, you can watch my dating playlist here.